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Jackson Park Highlands
Real Estate and Neighborhood Information

Jackson Park Highlands Overview

Jackson Park Highlands is a part of South Shore.

Jackson Park Highlands, one of the most historic and attractive neighborhoods in the south side of Chicago, is situated in a small pocket of the larger South Shore community that rests next door to scenic Jackson Park. Beautiful Victorian era mansions are commonplace in Jackson Park Highlands. Instead of tightly-packed rows of houses, these grand homes are spread out atop oversized green grass lots with matured trees and privacy hedges separating the properties even more. Not all real estate in Jackson Park Highlands is up market, there are also very nice mid-century split-levels and redbrick courtyard condominiums that provide ample living space for couples and families with smaller budgets.

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As a result of its historically exclusive status, today the tree-lined residential streets of Jackson Park Highlands offer some of Chicago’s largest and most attractive properties in the city. Of course, with the prestige of living in such an elegant neighborhood, homebuyers can expect the real estate here to be some of the more expensive on the south side.

The immense detached single-family dwellings that sit on large green lots are most common in the neighborhood, although several low-rise condo and apartment buildings were erected in the area in the 1950s and ‘60s. The main multi-unit residential buildings are mostly along Jackson Park Highlands’ wide border thoroughfares. The massive vintage-style, redbrick courtyard condominiums typically offer one-, two-, and three-bedroom units that range in price from to the mid $100,000s to the low $200,000s.

Several of Jackson Park Highlands’ beautiful houses, built in the early 1900s, would be considered mansions by today’s standards and continue to maintain the awe-inspiring grandeur. One of the great design approaches used by the architects of the neighborhood’s residences of the time period was to construct these homes set back on 50-foot-wide plots of land leaving generous front lawn space and room for faultlessly trimmed hedges and wrought-iron front gates. Such features were innovative at the time, and were later incorporated into typical suburban neighborhood planning. Other infrastructural advancements enjoyed by the residents of Jackson Park Highlands back in its emergence were the use of underground utilities and—most notably—it is one of the only Chicago neighborhoods that doesn’t have alleys between streets.

There is a wide variety of homes in the Jackson Park Highlands that span from towering three-story Victorians with room-size pillared porches and back garages to more modern split-levels with attached garages. All in all, the properties in this once elite south side Chicago neighborhood are impressively magnificent with a timeless charm that persists throughout the years. Detached single-family houses in Jackson Park Highlands start in the low $300,000s, but the price tag for many of these century-old homes can easily be in the $700,000 or $800,000 range.

Jackson Park Highlands History

The history of Jackson Park Highlands is a classic story of gentrification on Chicago’s south side. Like most of the surrounding area, the fate of Jackson Park Highlands was intimately linked to the success of the World’s Columbian Exposition that was held just to the north in Hyde Park in 1893. The neighborhood had only been annexed by the city of Chicago about four years prior to the World’s Fair, so at the time it was still little more than a near south suburb.

The Columbian Exposition was a resounding success, drawing more than 25 million visitors to the region. With dramatic increases in both traffic and attention, property values in the South Shore region appreciated dramatically. The development of Jackson Park Highlands, however, did not result from raising property values; instead, it was the result of Protestant 'white flight' from the nearby Washington Park neighborhood that was faced with a large influx of African American families who were moving to the Chicago area from the South. The Protestants started developing and settling the land in Jackson Park Highlands between the turn of the century and 1905, carefully crafting it as an exclusive oasis on the southern edge of the sprawling grounds of Jackson Park.

In 1906, the residents of Jackson Park Highlands opened the South Shore Country Club, a garish and fancy complex located on a 67-acre plot of lakeshore property. The exterior of the country club was designed in Mediterranean Revival style, an architectural genre rarely seen in the Midwest. The club was built by the Marshall & Fox firm, which is also credited with the Blackstone Hotel and the Drake Hotel in downtown Chicago. The man that conceived of the resort, Lawrence Heyworth, had the good fortune of timing the club’s opening with the closing of another golf course in nearby Washington Park. As a result, Heyworth had little trouble gaining enough money and public support to go through with the project.

Jackson Park Highlands is a place of single-family homes a lot like neighboring Hyde Park or Kenwood. In the decade after the Jackson Park settlement was formed, all of the South Shore community experienced an influx of new arrivals and a subsequent housing boom. The area was populated by middle and working-class Jews and African Americans, as well as Irish, Swedish and German immigrants. The South Shore boom bolstered the seclusion of the Jackson Park highlands community, as the neighborhood was nicer and its residents were considerably wealthier than those moving into the surrounding neighborhood. That status has continued throughout the 20th century, as several famous Chicagoans have lived in Jackson Park Highlands, including activist Reverend Jesse Jackson, rocker Bo Diddly, and pro football player Gale Sayers.

Dream Town Knows Jackson Park Highlands

As Chicago neighborhood experts, Dream Town has successfully sold properties in Jackson Park Highlands. Dream Town holds a well-earned reputation for its impressive sales volume and dedication to personal, attentive service. Benefit from the Dream Town advantage when selling your Jackson Park Highlands home. Utilizing state-of-the-art technology, Dream Town drives more sales than any other Chicago brokerage.

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The Sights of Jackson Park Highlands

Jackson Park Highlands Neighborhood Photo
Jackson Park Highlands Neighborhood Photo
Jackson Park Highlands Neighborhood Photo

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Schools In The Jackson Park Highlands Area

See grade levels, address, and scores for schools in the Jackson Park Highlands area.

School Type Grade Rating

Avalon Park Elementary School

8045 South Kenwood Ave - public

Preschool - Middle PK-8
2

Bradwell Community Arts & Sci Elementary School

7736 South Burnham Ave - public

Preschool - Middle PK-8
2

Bouchet Elementary Math & Science Academy

7355 South Jeffery Blvd - public

Preschool - Middle PK-8
3

Fiske Elementary School

6020 South Langley Ave - public

Preschool - Middle PK-8
1

Mann Elementary School

8050 South Chappel Ave - public

Preschool - Middle PK-8
1

Murray Elementary Language Academy

5335 South Kenwood Ave - public

Elementary - Middle K-8
5

Okeeffe Elementary School

6940 South Merrill Ave - public

Preschool - Middle PK-8
2

Ray Elementary School

5631 South Kimbark Avenue - public

Preschool - Elementary PK-7
5

Revere Elementary School

1010 East 72nd St - public

Preschool - Middle PK-8
2

Wadsworth PreK-8th STEM School

6650 S. Ellis Avenue - public

Preschool - Middle PK-5
3

Sexton Elementary School

6020 South Langley Ave - public

Preschool - Middle PK-8
NR

Mt Carmel High School

6410 South Dante Avenue - private

High 9-12
NR

South Central Community Services - South Shore

7550 South Phillips Avenue - private

Elementary - High 4-12
NR

Sonia Shankman Orthogenic School

1365 East 60th Street - private

Elementary - High 3-12
NR

Sonia Shankman Orthogenic-Day

1365 East 60th Street - private

Elementary - High n/a
NR

Sonia Shankman Orthogenic - Int

1365 East 60th Street - private

Elementary - High n/a
NR

Dulles Elementary School

6311 South Calumet Ave - public

Preschool - Middle PK-8
1

Hirsch Metropolitan High School

7740 South Ingleside Ave - public

High 9-12
1

Park Manor Elementary School

7037 South Rhodes Ave - public

Preschool - Middle PK-8
2

Tanner Elementary School

7350 South Evans Ave - public

Preschool - Middle PK-8
2

School data provided by GreatSchools.School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly. GreatSchools Ratings provided by GreatSchools.org.

Surrounding Neighborhoods

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